Two, you'll have a much easier time obtaining a mortgage product if you have a track record of W2 income.In the meantime, continue implementing the strategies you mentioned: save religiously, build your credit, pay any existing debt owed, etc.

Tenants save money when using a shared meter, so there's plenty of room for error when calculating how to distribute the charges.

Each property has two savings accounts - security deposit & reserves, and one checking - mortgage payments and utilities 

Avoiding errors and being educated on the laws can save time, money, and potential legal challenges.

Wrapping 3 properties into one blanket loan shouldn't be a problem, save these are sitting on any sizeable acreage.You might get lucky and find a unicorn local bank or credit union that would consider that kind of leverage, but I would say overall, those terms are very unrealistic.Cheers!

Do you think it's better to start sooner with a cheaper property to get in, or potentially wait longer to save more? 

You have NO leverage, no matter what he builds or does not build, except for the developer saving some money in legal fees and cutting down on mesne profits damages.

Considering your situation, I would try to find deals on Facebook, saved zillow/realtor search notifications, etc.

I poured my life saving into it and make it a duplex.

Key provisions like bonus depreciation, the 20% pass-through deduction, and 1031 exchanges have saved investors thousands of dollars each year.